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1.
Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date. 相似文献
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Biswanath Das Boyapati Veeranjaneyulu Penagaluri Balasubramanyam Malampati Srilatha 《Tetrahedron: Asymmetry》2010,21(23):2762-2767
The stereoselective total synthesis of two naturally occurring α-pyrone derivatives, (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decanyl]-5,6-dihydro-2H-2-pyrone has been accomplished involving the Sharpless kinetic resolution and olefin cross-metathesis as the key reactions. 相似文献
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A stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one is reported. The strategy utilizes an iterative Jacobsen hydrolytic kinetic resolution, ring opening with a chiral propargylic synthon and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps. 相似文献
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《Tetrahedron: Asymmetry》2007,18(18):2197-2200
A stereoselective synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one is reported. The strategy utilizes an olefin cross-metathesis, syn-benzylidene acetal formation and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps. 相似文献
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An organocatalytic enantioselective synthesis of the title compounds has been achieved. The stereogenic centers were generated by the iterative use of proline catalyzed α-aminoxylations and HWE olefination of aldehydes while the lactone ring was constructed by ring closing metathesis. 相似文献
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S. Chandrasekhar Ch. Narsihmulu S. Shameem Sultana M. Srinivasa Reddy 《Tetrahedron letters》2004,45(50):9299-9301
Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia. 相似文献
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A chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2H-pyran-2-one using bromobenzene as a starting material is presented. This important structural motif is found in a large number of chiral lactones that present a wide range of biological activities. The key features of the preparation include enzymatic dioxygenation of bromobenzene using Escherichia coli JM109 (pDTG601), microwave-assisted acyloin cleavage, and tin mediated lactonization. The stereochemical assignment for the alcohol was confirmed by NMR analysis of Moshe?s derivatives. 相似文献
10.
The title compound was prepared by the condensation of 4,6-diphenyl-2H-pyran-2-one and acetophenone in phosphorus oxychloride. The absorption spectrum of this 2,2-methine dye is compared with those of the corresponding 2,4- and 4,4-methine dyes. 相似文献
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F. Makaev L. Bets L. Vlad S. Pogrebnoi A. Barba A. Besolov S. Malinovskii R. Lyubodarskii 《Russian Journal of Organic Chemistry》2006,42(6):849-854
A procedure was developed for the stereoselective synthesis of aminated derivatives of (+)-1-{(1R,3R,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-yl}ethan-1-one. The configuration of the side-chain chiral center in (+)-1-{(1R,3R,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-yl}ethan-1-ol was determined by X-ray analysis. Diketene and Meldrum’s acid were proposed as initial compounds for the synthesis of, respectively, 3-oxobutanoic and malonic acid esters having a 1-ethyl-4,7,7-trimethylbicyclo[4.1.0]hept-4-ene fragment. 相似文献
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Stereoselective total synthesis of α,β-unsaturated lactone (1a), isolated from Ravensara crassifolia, has been achieved efficiently starting from chiral 2,3-O-isopropylidene-d-glyceraldehyde (3) followed by asymmetric allylation and ring-closing metathesis. The antiproliferative activities of compounds 1a, 1b and the unusual bicyclic compound 2 were evaluated against three-cancer cell lines, THP-1 and U-937 (leukemia) and A-375 (melanoma). 相似文献
13.
I. V. Mineeva 《Russian Journal of Organic Chemistry》2013,49(2):253-258
A simple and efficient asymmetrical synthesis was performed of a convenient bifunctional building block, methyl (R)-5,5-dimethoxy-3-methylpentanoate and its (S)-enantiomer. The possibility was shown of its application to the synthesis of insect pheromones. 相似文献
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The first efficient total syntheses of rugulactone and 6(R)-(4′-oxopent-2′-enyl)-5,6-dihydro-2H-pyran-2-one have been achieved in six steps with 51% and 48% overall yield, respectively. The key steps are Jacobsen’s hydrolytic kinetic resolution (HKR), Horner-Wadsworth-Emmons (HWE) homologation, and ring-closing metathesis reaction. 相似文献
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Giafranco Cainelli Michele Contento Daria Giacomini Mauro Panunzio 《Tetrahedron letters》1985,26(7):937-940
A total stereocontrolled synthesis of (), an intermediate in the synthesis of (+)-thienamycin, carbapenems and penems, based on a strategy that uses the S(-)hydroxy ethylbutyrate as chiral building block, is reported. 相似文献
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Kim DH Hwang JS Baek HS Kim KJ Lee BG Chang I Kang HH Lee OS 《Chemical & pharmaceutical bulletin》2003,51(2):113-116
A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one (Kojyl-APPA), was synthesized in good yield. The effects of Kojyl-APPA on tyrosinase activity and melanin synthesis were investigated. Kojyl-APPA showed tyrosinase inhibition effect (30%) in situ, but not in vitro. Kojyl-APPA inhibited tyrosinase activity significantly at 24 h after treatment in normal human melanocytes. It means that Kojyl-APPA is not a direct inhibitor of tyrosinase itself, but it is converted to a potential inhibitor kojic acid enzymatically in cells. In addition, Kojyl-APPA decreased melanin content to 75% of control in melanoma cells and decreased neomelanin synthesis to 43% of control in normal human melanocytes. Its permeation through skin increased by about 8 times as compared with kojic acid. 相似文献
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I. V. Mineeva 《Russian Journal of Organic Chemistry》2013,49(5):712-716
A simple and efficient asymmetric synthesis was performed of (+)-(S)-7,8-dihydrokanian and (4R,6R)-4-hydroxy-6-(2-phenylethyl)tetrahydro-2H-pyran-2-one involving Keck allylation in the key stage of building up the carbon scaffold of the target molecules. 相似文献